Publication: Synthesis of the Tetrahydropyran Fragment of Bistramide D
Issued Date
2014-01-01
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ISSN
21935807
21935807
21935807
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2-s2.0-84903777289
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Mahidol University
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SCOPUS
Bibliographic Citation
Asian Journal of Organic Chemistry. Vol.3, No.7 (2014), 792-796
Suggested Citation
Roderick W. Bates, Lu Li, Kalpana Palani, Wanida Phetsang, Joanna Kejun Loh Synthesis of the Tetrahydropyran Fragment of Bistramide D. Asian Journal of Organic Chemistry. Vol.3, No.7 (2014), 792-796. doi:10.1002/ajoc.201402052 Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/33647
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Title
Synthesis of the Tetrahydropyran Fragment of Bistramide D
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Abstract
A synthesis of the tetrahydropyran (THP) moiety of bistramideD has been completed by using cross-metathesis and kinetically controlled intramolecular oxa-Michael addition to form the ring with excellent trans selectivity. The C9 methyl substituent was introduced by using an unsaturated sulfone building block, which can be most effectively prepared through a combination of diastereoselective allylation and alkene isomerisation. The effect of this methyl group on subsequent cross-metathesis reactions can be mitigated by careful choice of reaction conditions. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.